JPH0214924B2 - - Google Patents

Info

Publication number: JPH0214924B2
Authority: JP; Japan
Prior art keywords: acid; sialic acid; immobilized; water; aqueous solution
Prior art date: 1982-08-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP57145563A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5936102A (ja

Inventor

Isatake Matsumoto

Aryasu Shibata

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Seikagaku Corp

Original Assignee

Seikagaku Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-08-24

Filing date

1982-08-24

Publication date

1990-04-10

1982-08-24 Application filed by Seikagaku Corp filed Critical Seikagaku Corp

1982-08-24 Priority to JP57145563A priority Critical patent/JPS5936102A/ja

1984-02-28 Publication of JPS5936102A publication Critical patent/JPS5936102A/ja

1990-04-10 Publication of JPH0214924B2 publication Critical patent/JPH0214924B2/ja

Status Granted legal-status Critical Current

Links

SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims description 32
SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 claims description 31
239000000126 substance Substances 0.000 claims description 11
239000003463 adsorbent Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 8
229920000642 polymer Polymers 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
DUUGKQCEGZLZNO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Chemical compound C1=C(O)C=C2C(CC(=O)O)=CNC2=C1 DUUGKQCEGZLZNO-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
RVWZUOPFHTYIEO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Natural products C1=C(O)C=C2C(C(=O)O)=CNC2=C1 RVWZUOPFHTYIEO-UHFFFAOYSA-N 0.000 description 18
239000003310 5-hydroxyindoleacetic acid Substances 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 18
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 14
238000005406 washing Methods 0.000 description 13
LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical group OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 11
229940000681 5-hydroxytryptophan Drugs 0.000 description 11
LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 11
238000000926 separation method Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
229920000936 Agarose Polymers 0.000 description 9
238000000746 purification Methods 0.000 description 9
SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 7
210000000601 blood cell Anatomy 0.000 description 7
239000011521 glass Substances 0.000 description 7
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
239000004593 Epoxy Substances 0.000 description 6
-1 carbodiimide compound Chemical class 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
102000004169 proteins and genes Human genes 0.000 description 6
108090000623 proteins and genes Proteins 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 5
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 3
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 3
102000002068 Glycopeptides Human genes 0.000 description 3
108010015899 Glycopeptides Proteins 0.000 description 3
108090001090 Lectins Proteins 0.000 description 3
102000004856 Lectins Human genes 0.000 description 3
102000005348 Neuraminidase Human genes 0.000 description 3
108010006232 Neuraminidase Proteins 0.000 description 3
102000007365 Sialoglycoproteins Human genes 0.000 description 3
108010032838 Sialoglycoproteins Proteins 0.000 description 3
239000002253 acid Substances 0.000 description 3
IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
210000003743 erythrocyte Anatomy 0.000 description 3
150000002270 gangliosides Chemical class 0.000 description 3
239000002523 lectin Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000001179 sorption measurement Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
241001529572 Chaceon affinis Species 0.000 description 2
102000003951 Erythropoietin Human genes 0.000 description 2
108090000394 Erythropoietin Proteins 0.000 description 2
102000012673 Follicle Stimulating Hormone Human genes 0.000 description 2
108010079345 Follicle Stimulating Hormone Proteins 0.000 description 2
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
108091005804 Peptidases Proteins 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
239000004365 Protease Substances 0.000 description 2
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 2
ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 2
241000194017 Streptococcus Species 0.000 description 2
102000009843 Thyroglobulin Human genes 0.000 description 2
108010034949 Thyroglobulin Proteins 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
230000024245 cell differentiation Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
229940105423 erythropoietin Drugs 0.000 description 2
229940028334 follicle stimulating hormone Drugs 0.000 description 2
239000003349 gelling agent Substances 0.000 description 2
229960000587 glutaral Drugs 0.000 description 2
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
239000005556 hormone Substances 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
239000003446 ligand Substances 0.000 description 2
229920001542 oligosaccharide Polymers 0.000 description 2
150000002482 oligosaccharides Chemical class 0.000 description 2
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 2
102000004196 processed proteins & peptides Human genes 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
229960004025 sodium salicylate Drugs 0.000 description 2
229940014800 succinic anhydride Drugs 0.000 description 2
229960002175 thyroglobulin Drugs 0.000 description 2
ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-N 0.000 description 1
SNVRDQORMVVQBI-OWOJBTEDSA-N (e)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C\C(=O)NN SNVRDQORMVVQBI-OWOJBTEDSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
SNVRDQORMVVQBI-UPHRSURJSA-N (z)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C/C(=O)NN SNVRDQORMVVQBI-UPHRSURJSA-N 0.000 description 1
UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
VLKXLWGYPOUERV-UHFFFAOYSA-N 2-[3-(oxiran-2-ylmethoxy)propoxymethyl]oxirane Chemical compound C1OC1COCCCOCC1CO1 VLKXLWGYPOUERV-UHFFFAOYSA-N 0.000 description 1
SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
CAYJDIDYXCENIR-UHFFFAOYSA-N 2-[5-(oxiran-2-ylmethoxy)pentoxymethyl]oxirane Chemical compound C1OC1COCCCCCOCC1CO1 CAYJDIDYXCENIR-UHFFFAOYSA-N 0.000 description 1
WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
OIZGSVFYNBZVIK-FHHHURIISA-N 3'-sialyllactose Chemical compound O1[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](O)C[C@@]1(C(O)=O)O[C@@H]1[C@@H](O)[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@@H]1O OIZGSVFYNBZVIK-FHHHURIISA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
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OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
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ZWLFGLCGZUVIEA-UHFFFAOYSA-N nonanedihydrazide Chemical compound NNC(=O)CCCCCCCC(=O)NN ZWLFGLCGZUVIEA-UHFFFAOYSA-N 0.000 description 1
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238000004448 titration Methods 0.000 description 1
239000012581 transferrin Substances 0.000 description 1
210000002700 urine Anatomy 0.000 description 1

Landscapes

Saccharide Compounds (AREA)
Indole Compounds (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Investigating Or Analysing Biological Materials (AREA)

JP57145563A 1982-08-24 1982-08-24 シアル酸又はシアル酸含有物質の分離・精製法 Granted JPS5936102A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP57145563A JPS5936102A (ja)	1982-08-24	1982-08-24	シアル酸又はシアル酸含有物質の分離・精製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57145563A JPS5936102A (ja)	1982-08-24	1982-08-24	シアル酸又はシアル酸含有物質の分離・精製法

Publications (2)

Publication Number	Publication Date
JPS5936102A JPS5936102A (ja)	1984-02-28
JPH0214924B2 true JPH0214924B2 (de)	1990-04-10

Family

ID=15388025

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57145563A Granted JPS5936102A (ja)	1982-08-24	1982-08-24	シアル酸又はシアル酸含有物質の分離・精製法

Country Status (1)

Country	Link
JP (1)	JPS5936102A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI466897B (zh) *	2005-07-19	2015-01-01	Glytech Inc	癌細胞之檢測方法、糖鏈之構造解析方法，以及糖鏈衍生物

1982
- 1982-08-24 JP JP57145563A patent/JPS5936102A/ja active Granted

Also Published As

Publication number	Publication date
JPS5936102A (ja)	1984-02-28

Publication	Publication Date	Title
US5092992A (en)	1992-03-03	Polyethyleneimine matrixes for affinity chromatography
US3947352A (en)	1976-03-30	Polysaccharide matrices for use as adsorbents in affinity chromatography techniques
US4308254A (en)	1981-12-29	Material able to fix reversibly biologial macromolecules, its preparation and its application
US4423158A (en)	1983-12-27	Ion adsorbent for metals having a coordination number greater than two
JPH037681B2 (de)	1991-02-04
EP0308239A2 (de)	1989-03-22	Methode zur Verminderung der bakteriellen Verseuchung von Endotoxinen in Lösungen von Makromolekülen
US5085779A (en)	1992-02-04	Polyethyleneimine matrixes for affinity chromatography
JPS61272202A (ja)	1986-12-02	アフイニテイクロマトグラフイ用材料の製法
Nadkarni et al.	1994	Directional immobilization of heparin onto beaded supports
JPH0626667B2 (ja)	1994-04-13	サイクロデキストリン吸着材及びその用途
DE102006055558A1 (de)	2007-05-31	Endotoxinadsorber und Verfahren zur Entfernung von Endotoxin unter dessen Verwendung
JPS5853757A (ja)	1983-03-30	免疫アフイニテイクロマトグラフイ−用吸着体及びその製法
JPH0427504B2 (de)	1992-05-12
JPH0116389B2 (de)	1989-03-24
CN103933947B (zh)	2015-10-14	用于清除类风湿因子的血液净化材料及其制备方法
EP1507563B1 (de)	2008-11-26	Endotoxin-bindende liganden und ihre verwendung
JP2511500B2 (ja)	1996-06-26	胎盤組織タンパク質ｐｐ▲下４▼の精製法
JPH0214924B2 (de)	1990-04-10
EP0403700B1 (de)	1992-08-05	Polyethylenimin-Matrizen für Affinitätschromatographie
EP0268997A1 (de)	1988-06-01	Verfahren zur Isolierung und Reinigung von Cyclodextrinen
JPH11152330A (ja)	1999-06-08	ポリリジン、及びポリリジンの製造方法、及びポリリジン組成物、及びエンドトキシンを除去する医薬品の生産方法
JPH0147997B2 (de)	1989-10-17
JPH0553802B2 (de)	1993-08-11
JPS6348451A (ja)	1988-03-01	クロマトグラフイ−用吸着担体
JPS606191A (ja)	1985-01-12	低分子ウロキナ−ゼと高分子ウロキナ−ゼの分離方法